The comment about leaving a "tall stump" to push on is excellent. You should definitely search TBN for posts about clearing land, stump removal, etc. In fact, the compact grapple video on Everything Attachments adds to the knowledge base plus there are lots of videos on Youtube.
I highly recommend hiring dozers when it is called for, but it sure sounds like what you want to do can be done easily enough with a tractor.
Buy the tractor and do it yourself would be my vote.
I am beginner with some background around construction, bought a tractor this summer for our place, and love doing these things myself. Do not be surprised how much skill and technique there is to learn in using a tractor, FEL, and box blade to clear and shape land. I prefer to read up on TBN, find some videos, and then get to it on my own tractor. It helps to have patience and practice and a willingness to mess it up a little before getting it right. :laughing: